Birth of the cool

The laid-back and effortlessly stylish look pioneered by the jazz greats began life in a side-street store, writes Josh Sims

He is adjusting the collar on a shirt – navy or maybe black, with white buttons. More unexpectedly, he is wearing an Alpine-style hat, high, narrow-brimmed, with badges. What would look comical on anyone else looks effortlessly right on him. But then this 1956 black and white photo is of saxophonist Gerry Mulligan, looking into a dressing-room mirror. He’s a cool dude in a cool era. What is perhaps stranger is where that dressing room is: not in one of the high fashion hubs of London or Paris, not Milan or even New York – but in a small, side-street store in Cambridge. And that’s Cambridge, Massachusetts.

Here was found Charlie Davidson’s The Andover Shop. It was here where Ivy League style took hold, where the WASPish under-graduates of Harvard, Princeton or Columbia developed a none too formal, nor too casual style of dress that would arguably become the lynchpin for western male sartorial standards for the next half century and more: crisp white button-down Oxford shirts and army surplus khakis, saddle shoes and penny loafers, hopsack blazers and flannel trousers, knit and rep ties and shawl-collar cardigans. It was, defiantly, the look of good grooming, privilege and money. It was defiantly white. That worked for Mulligan. But then what would fellow jazz maestro Miles Davis also be doing there, in everything – background, race, culture – an outsider? Or John Coltrane? They were, in the words of Roy Haynes, also a visitor, just picking up the “slickest shit out”.

Jazz has long been associated with ideas of cool, and a cool that is not just this week’s fashion, but which comes from the core, that grows out of living apart from the mainstream, from going one’s own way – it’s the cool of a James Dean, Steve McQueen or Cary Grant, sometimes imagined, sometimes projected (“Everybody wants to be Cary Grant,” noted Cary Grant. “Even I want to be Cary Grant”) but often innate. Certainly, the great players of jazz from the 1950s to 1960s – chiming with post-war prosperity, the birth of the teenager, the civil rights movement and the spread of TV as a mass media – effectively invented the modern idea of cool that would later inform the performances and personae of Dean, McQueen et al.

It was Capitol Records that, in the year before Mulligan’s snap, helped popularise the term with its album ‘Classics in Jazz: Cool and Quiet’, Davis underscoring the ineffable definition of this ever-so-desirable state of being with his seminal ‘Birth of the Cool’ compilation in 1957. By association with its performers, and their performances – in smoky, ill-lit, intimate late night venues, immortalised in evocative monochrome photography – ‘cool’ came to be associated with the idea of a nonchalant manner and effortless style, as much in playing as in posing. More than any record label before or since, the visual style of Blue Note in particular – boldly typographic, modernistic, unexpected and unmistakable, and perhaps the first to match the artfulness of sleeve design to that of the music – drove this home. Its most striking aspect, its colour-wash, stained glass effect appropriately gave its subjects the power of saint-like iconography.

But the clothes had to match, in part to sell the complexity of the music. And what better way for a sound that was radical than duds that also cut against the grain – by appropriating the uniform of the conservative, by undercutting the US national power-broking tribe much as Teddy Boys were doing in the UK, taking the style of one’s betters and, well, making it better? The result was more than a gravitational pull for pioneering jazzmen to the east coast caucasian enclave, and this one little shop of collars, cuffs and clubhouse rules. It was, appropriately enough, the meeting of dissonant notes, of the establishment and the experimental, the square and the hip, to create as much a new aesthetic of style as of sound.

Yes, the style-seeking jazzmen were building on the shoulders of swing and bebop giants – Louis Armstrong and Duke Ellington were none too sloppy with their wardrobes either. Billy Eckstine - whose big band extraordinarily hot-housed the talents of Dizzy Gillespie, Art Blakey, Charlie Parker and Miles Davis among others – even designed and wore his own collar shape, the ‘Mr. B’, a high-roll collar that (with some imagination) formed a ‘B’ shape over a Windsor-knot. But the simplicity of the newly-adopted and twisted Ivy style perhaps only made the post-trad music feel all the more avant-garde.

And the music came first. Far from being unpracticed, unnatural wonders with their instruments, the likes of Davis and Coltrane, Mulligan and Haynes, as well as Bill Evans, Charles Mingus, J.J. Johnson, Paul Desmond and other dedicated musicians of the period, had given recitals since childhood – and for these they were expected to dress presentably, which back then meant like their parents, as adults-before-their-time, in scaled down takes on the era’s wide-shouldered, peak-collared suiting. It was a habit that stuck, as visits to The Andover Shop – or the likes of J.Press, as favoured by Ahmet Ertegun, the co-founder of Atlantic Records – would refine. What these jazz masters wore, often as signatures, consequently attained an unexpected hispster credibility: Dizzy Gillespie’s double-breasted pinstripes, goatee, black horn-rimmed glasses and beret; Stan Getz’s dark Italian suits and skinny ties; Lester Young’s tilted pork-pie hat; Thelonius Monk, with his outsized specs and beret too... Oh how they loved a hat, belonging to a period when any self-respecting man about town would risk social opprobrium to go about without one, even if in not so studiedly unstudied a way.

Then there was Miles Davis. It was Davis – searching for a look to announce his cleaned-up comeback – who made the clarion call to this definitive, artsy, neo-con jazz dress when, in 1954, the aptly-named jazz promoter Charles Bourgeois took him to the Cambridge haberdasher to find what he would call Davis’ “costume”. The trumpet player left having put the I back into Ivy, with his own distinctive blend of soft-shouldered, narrow-lapeled tweeds and madras jackets, blindingly-white button-downs, flannels and Bass Weejuns.

The following year, playing the Newport Jazz Festival, he took to the stage in a custom-made, side-vented seersucker sack coat, club-collared shirt and a bow-tie.

Described thus, he could have looked like a pre-war door-to-door salesman, stiff and falsely smiling. He looked anything but. He looked like a man of tomorrow. Six years later, in fact, he was being hailed by ‘Esquire’ as a model of style for his bespoke suits, made by Emsley in New York and costing him a whopping $185 a pop. Bourgeois similarly overhauled Chet Baker - who, as the promoter would put it, “arrived from California dressed like a ragamuffin”, also in 1954 - and again at the same store. In 1958 the cover of ‘Chet Baker in New York’ – note the title, pointedly east coast, against the bohemian and badly-dressed west coast – had him in rep tie, white button-down and navy blazer, his hair slicked back.

We’re decidedly not in Baker’s hometown of Yale, Oklahoma anymore – more Yale, Connecticut, home of the elite training ground of American blue-bloods. Later Baker would adopt a trademark minimalistic dark suit and white t-shirt – at a time when tailoring played only to the accompaniment of shirt and tie.

Like all moments in style this great era of jazz cool was, of course, set to pass – not least because the jazzmen’s way with a button-hole, tie-pin or pleat, just so, would enter the dress vernacular. It would become, superficially at least, the norm. They moved with fashion too, so that by the 1960s Davis, for one – how the great had fallen - preferred kick flares and fey neck-scarves. And, naturally enough, they got older and their outlook changed. Maybe, as the world grew ever more obsessed with image, at the expense of content, these maestros felt less and less like dressing the part.

The legacy lingered, with the likes of Wynton Marsalis, who in the 1980s rocked 40s elegance when everyone else was rolling their jacket sleeves and forgetting to put on socks. And, as the fashion business has acknowledged, it lingers in jazzland even today: among the notables, David Sanchez – who’s modelled for Banana Republic, Joshua Redman – who’s modelled for Donna Karan, and Greg Osby - who chiefly just models his own vintage fedora but, like Mulligan with that Bavarian number, just looks straight-from-the-fridge dad.

But, the music aside, the greatest legacy goes beyond jazz. Jazz’s lifting and re-energising of Ivy style gave men a model of cool that is timeless. It is for less well-dressed men to, as Charles Mingus had it, look to its golden era of style and “sing their praises while stealing their phrases”.